Heartbreakingly Perfect
by the lights of paris
Summary: UN-COMPLETED. WILL NOT BE COMPLETED FOR THE TIME BEING.
1. Prolouge

**Title: **Heartbreakingly Perfect

**Summary: **Choices are made and hearts are broken. Paper gets crumpled up, mistakes can't be erased. Two paths cross and fireworks explode. People are messed with, people fire guns. Pull the trigger and I'm all yours. People forgive and forget, some hold grudges and try and get revenge. History is pulled up from the past and people are in _big _trouble. Post 6.1O.

**Authors Note: **I shouldn't be starting a new story seeing as I have two too actually finish. One of which, I don't think I ever will and another one I need to be inspired, to be able too finish. This is set a year after the five year flash forward. It's short and choppy and doesn't make a lot of sense at the moment. It's basically just trying too explain what's happened. Come in future chapters, you'll notice I may of changed certain things about the flash forward (or invented things that may of happened). It covers the couples mentioned below heavily but it doesn't mean that they'll actually be _together_ during the story and it isn't limited to just these couples although I doubt I'll do any others.

**Couples: **Serena\Nate, Jenny\Nate, Jenny\OC, Serena\Dan, Chuck\Blair, Jack\Georgina, Rufus\Lily, Dan\Vanessa, Vanessa\OC, Carter\OC, Carter\Serena.

**Disclaimer: **I own nothing.

* * *

**PROLOUGE**

* * *

Serena shook her head, tears flowing out of her eyes. Mouth flies up too her mouth and a strangled cry comes out. This couldn't be happening. No. It's not true, this couldn't be happening too her. She stomps her feet and screams at the doctor telling them that this is a mistake. That they have it wrong. This can't be true. A pair of arms wrap around her waist, trying too keep her still. She thrashes around, and screams and yells and cries. They all must be lying. It's not true, it can't be. Everybody's just messing with her. It's just a big joke and she's the punch-line. Blair's going too smile at any second and scream out: Happy April First. But she doesn't. Nobody does. Eventually she stops. She slumps against the wall, knees at her waist and head in her hands. Her blonde hair spilling out around her. She can't cry anymore. She's used it all up, her eyes are dry. Her voice is weak and she can barely speak but she doesn't care. She doesn't care that's she's a mess, that her clothes are crumpled, or that her makeups run. She doesn't care that she's making a fool of herself. She just wants to go home and curl up in a ball and act like this is a dream. She wants too wake up the day before the Shepard Wedding. Then nothing of this would of ever happened. Everything would be okay, everything would be normal. What's normal, anymore? Nothing. That's what. Her heart aches and yearns for her baby girl. Her baby girl which was ripped away from her too soon. Her baby girl which only got too see the world for a few minutes before being taken away from her. It's not fair that she gets too live her life and her baby doesn't. Nate finally arrives. He slumps down next too her and lets the tears free that's he's been holding on to. They decide too go home and when they do they both break down again. They supply enough tears for a flood. Everything in their house is a reminder of the little girl they had just lost, of the life they could of had, _would of had. _All Serena wants to do is run, she wants too run away, away from the Upper East Side, away from New York, away from America. She just wants too keep on running, never stopping but she can't.

* * *

"I wonder how she's doing." Dan says quietly. Rufus sighs and puts a hand on his son's shoulder. Serena hadn't spoken too him for exactly four days. She hadn't spoken too anybody, nobody had heard from her since she lost the baby. She was starting too scare Dan, even if he hated her and wanted nothing to do with her, he still loved her and still cared about her and he still wanted to know how she was doing.

"She'll be fine, Dan." Jenny responded, waving her hands up in the air like it was no big deal. He glared at his younger sister. Over the years Jenny and Serena had grown closer, finally, _finally_, getting on since the whole Nate thing of '1O but then his wife had to go and screw his little sister's boyfriend and that was enough for Jenny too want too plan her death.

"She lost her baby, Jen." Dan stated. Jenny only shrugged her shoulders. His mouth fell open in disbelief.

"Consider the baby lucky, that she wouldn't have Serena Van Der Woodsen as her mother." She replied, shaking her head in frustration as she tried too sew a hem that didn't want too co-operate.

"Stop being such a bitch, Jenny." Dan growled. He had really thought that Jenny was behind her "Queen Bitch Phase." That she had grown up and moved on because she had acted like she had for the past six years but now here she was turning back into her sixteen year old self. The one that Dan was ashamed of. Jenny ignored his comment, and kept on sewing. Dan sighed and pushed himself up off of the seat in the old Humphrey Loft. He had moved back in after the explosive mess that was Serena and Nate. The mess that had started three months into their marriage.

"Why do you even care so much, Dan? She cheated on you with your best friend who was dating your sister. She got knocked up with another man's child three months into your marriage and all she said too explain herself was "HE GETS ME DAN!" You need too stop caring about her because she stopped caring about you." Jenny states, looking at her brother's back. Rufus has stayed quiet through all of this, he didn't want too handle two children who despised his wife's eldest daughter.

"QUIET! BOTH OF YOU!" Rufus finally shouts. Exploding with anger.

"You two will have to forgive Serena. She's your step-sister and you two share not one sibling with her, but two now." Rufus is referring too the child that he and Lily recently had. After Serena and Dan got married, he and Lily had been talking and had a little too much too drink and ended up in a guestroom at the Bass's townhouse and had conceived a baby boy. As soon as their partners had found out, they had dumped them on the spot, calling them traitors and liars. Lily and Rufus had decided too get married and give each other another chance. It was a little strange considering at the time, their children were on their honeymoon. Rufus and Lily couldn't help but feel a little responsible for the break up of Serena and Dan but everybody had seen it coming, even little Jenny.

She didn't miss the longing looks Nate shot Serena, or how whenever her name was mentioned he would light up. She had seen it coming and yet she had chosen too ignore it. She was _this _close to becoming an Archibald. She didn't want to break up with Nate. She loved him and she would do anything to keep him. They had started dating a year after Dan told everyone he was Gossip Girl, ten months after Nate had broken up with Sage Spence. They had been engaged when he had chosen too bang Serena and he had broken Jenny's heart. She knew that Nate still had a thing for Serena but she never thought in a million years he would act on it while they were together, while they were _engaged!_ But he did. Dan might be so quick to forgive and forget but Jenny wasn't wired that way. She would never forgive the two blondes for what they had done too her family.

"I'm going to go home now and I expect the both of you too be nice too Serena when you see her and to stop this nonsense fighting." Rufus informed, before leaving the loft. Jenny sighed and Dan was quick too leave after his father, slamming the door behind him.

"YAY! Just Jenny here." She muttered under her breath.

* * *

Jack smirks as he watches Georgina show off her latest purchase from La Perla. She swishes back and forth in their bedroom, her hips swaying, her hair flying freely around her. The pair had just returned from Fiji. Their first trip away since they had Max. Baby Max technically wasn't really even a baby. He was two years old and the devil. He was also their youngest child. Meridith was their eldest at three years old and then there was Milo who was nine years old. Shortly after meeting Jack, Georgina had divorced Phil and had ran straight into Jack's arms. At first it was casual, no strings-attached but a wild night in Vegas changed all that when they widely and drunkenly eloped and were forced too grow up.

"Like?" She asks seductively. Placing her hands on his knees and raising an eyebrow up at him. He reaches forward and unhooks her bra.

"Love." He slyly replies, watching as her lacy forest green bra fell to the floor.

"Good." She says before pushing him backwards on the bed and climbing on top of him. He simply smiles in response, letting her take the lead.

* * *

Vanessa stares at the space around her. It's large and bare and tasteless. Her fiancee had picked it out upon their return too New York. While she was in Spain, she feel in love with an New York Native - George "Barcelona" Beets. Her and Barcelona had hit it off right away, although since she was still heartbroken over Dan, it had taken a few years - and the reveal of Dan being Gossip Girl - too bring the two together. She had decided too stay away from the marriage of Dan Humphrey and Serena Van Der Woodsen. She wasn't on good terms with either of them but then a year later, she had been offered a job offer in New York. Just like Barcelona had and now here they were. The two of them, standing in _their_ house.

"Do you like it?" He asks her. She nods her head even though she hates it. It's everything she hates but she can't bring herself too tell him that. Lately she's been lying too him a lot. She doesn't want him to judge her, doesn't want him to break of their engagement. It's stupid and she's Vanessa Abrams and Vanessa Abrams doesn't lie and she doesn't stay with a guy that she doesn't feel comfortable around but she _did _feel comfortable until three months ago when she heard that Dan and Serena had broke up. Apparently they had been for quite some time, she still didn't know why but she felt that if she stayed with Barcelona she was missing out on a chance of having Dan.

And that's why she won't leave Barcelona because she'll never have Dan and she doesn't want to give up on Barcelona.

* * *

"I need to report a missing child." Chuck says into the phone, never taking his eyes of of Blair. His Blair, who is curled up on their bed, shaking and sobbing and screaming.


	2. Wedding Bliss

**Title: **Heartbreakingly Perfect

**Summary: **Choices are made and hearts are broken. Paper gets crumpled up, mistakes can't be erased. Two paths cross and fireworks explode. People are messed with, people fire guns. Pull the trigger and I'm all yours. People forgive and forget, some hold grudges and try and get revenge. History is pulled up from the past and people are in _big _trouble. Post 6.1O.

**Authors Note: **So this is a short chapter. Sorry for the delay. Our laptop actually broke and we only just got a new one. This is heavy on Derena, which was really hard too write as well. I wrote a lot of this in a notebook and then typed it up. Also, just wondering, are the authors notes at the top annoying? Would you rather them be at the bottom? Does anyone actually read the A\N? If you do, could you leave it in a review? Thanks. So this chapter is set a year before the other one and is Serena and Dan's wedding. Includes some Henry cuteness and badly written speeches.

**Disclaimer: **I own nothing.

* * *

**WOUNDED SOUL  
**

* * *

ONE YEAR EARLIER

* * *

Dan grabbed his _wife, _oh how wonderful it was to refer too her as that, by the waist and placed a soft kiss on her lips like he had done a thousand, a million times before, but now she wasn't just his girlfriend. She was his _wife_, bound together for life. She giggled and threw her arms around his neck, responding to the kiss like she had a thousand, a million times before. They pulled apart when they heard whines from Henry telling them they were as bad as his parents. Serena lay her forehead against Dan's and sighed in contentment. She had never been happier, this past year after her and Dan had gotten back together once again, he had been perfect. No longer taking her for granted and treating her like a real princess and she felt complete and so when he asked for her hand she agreed. Her and Blair had spent months planning the perfect wedding. Jenny joining in towards the end, begging and pleading to be the one to design the dress. Serena wasn't sure at first, even now she and Jenny weren't on great terms, ironically Jenny and Blair were acting like they were besties, but Serena finally agreed. She was Dan's sister after all and she was a great designer and they were sort of on good terms, now that she thought about it. They had grown closer and were finally resembling something like friends. Now standing here, she knew she had made the right choice.

"I love you." Dan whispered, placing another kiss on her lips. Softer, warmer, quicker, gentler. It was fleeting and it was perfect.

"I love you too." Serena replied, pulling away from him and turning around too face her family and friends.

"AND I LOVE ALL OF YOU!" She exclaimed, giggling. She hadn't even had a single drop of champagne yet and she was already on cloud nine. Blair was dreading the moment she got alcohol in her system.

"Even me?" Henry shyly asked. He loved hearing people tell him how much they adored him, liked him, loved _him._ Chuck often boated he was attention whore. Like it was something to be _proud _of. Serena shook her head at her young nephew. Closing the distance between them as she took several steps forward and swooped the four year old up into her arms.

"Especially you!" She cried, planting kisses all over his face. He giggled, screaming that he was too old for kisses but doing nothing to stop them coming. After five minutes of this, Serena finally planted him on the floor, giving his a head a small pat. She then turned around, back to facing her _husband_, oh she had a _husband!_, she had sworn when she was much younger she would never marry due to her mother's many divorces. She never wanted her life too turn out as hers did, but now standing here in front of Dan, she couldn't imagine _anything_ ever going wrong between the two of them.

* * *

Hours had gone by and the wedding was in full swing. It was now however, time for the toasts. Serena was giddy with excitement. She had been looking forward to this moment all night, people were going too _gush _about how perfect she and Dan were for each other. Serena remembered the speech she had given for Chuck and Blair, five years prior.

_"Blair and Chuck, I can not tell you how happy I am for the two of you. You've both made it so far and no one could be more perfect for each other then you two are to the point where it's a little scary. You've gone through so many ups and downs but some how you've both come out of it all, stronger then ever and together. Six years ago if someone would of even mentioned the idea of you two not only together - but married - I would of laughed and then probably had a heart attack because the idea is so ridiculous but so perfect right. I wish the both of you all the happiness in the world and I hope, not only for your sake but for everybody's sake, that the two of you never getting a divorce or break-up or have a massive fight. I love the both of you and I want the two of you to be forever happy because I've seen you both when you haven't been together, and that's when your both at your saddest whereas when your are together, you both shine."_

She wanted someone to make a speech like that about her and Dan. She wanted it so badly, and now she would hopefully get it. She was practically bouncing in her seat as Blair stood up and clinked a spoon against her sparkling grape juice, apparently Henry had felt left out with being the only one drinking sparkling grape juice and so both Blair and Chuck had agreed too drink it as well, everybody fell silent as Blair gathered all the attention in the room.

"I would like to propose a toast too my best friend and her Humphrey," She began, shooting a smile in the direction of Serena and Dan. Laughs erupted from around the room, the old nickname not forgotten and still very frequently used, "Serena, Dan. I wish the both of you all the happiness in the world. Although, S, couldn't you of chosen someone more respectable too marry? I know your grandmother would of just _loved_ it if you married Carter," She joked, memories of Junior year flooding back too her mind. Serena had been so upset with Cece around that time unable too even comprehend what her grandmother saw in Carter Baizen that was anything better then Dan and then who dated him a few years later? "S, your my best friend and I love you with my whole heart and I just want you too be happy. It's what I've always wanted, even if I did want too destroy you at times. I'm glad that your happy even if Dan Humphrey from _Brooklyn_ contributed to that happiness. Dan, there was a brief time where we were friends. I would of gone as far as too call you one of my best friends, even if now we barely talk. I just want too tell you that if you ever dare too break Serena's heart again, I will personally build up a team too come and destroy you and trust me, it wouldn't be hard considering how many people actually hate you-"

"B!" Serena interrupted, exclaiming. She wanted a nice, lovely speech about how her and Dan were soul mates not a speech about how she should marry Carter Baizen and everyone hates her husband.

"Fine. Fine," Blair rolled her eyes, took a sip from her flute of sparkling grape juice and went back too her speech, "Anyway both of you have gotten back together and broken up more times then anyone can count. I think in the past five years alone you've had six break ups along with countless fights but you've both managed to make it to the aisle and tie the knot. I only hope that we won't be seeing divorce papers in a few months-"

"OK! B, maybe someone else could make a speech?" Serena suggested. Blair sighed and sat back down, Chuck's arm going around her shoulders and pulling her in closer. He placed a soft kiss on her forehead and whispered something along the lines of "That was great but wait until I make my speech." Nate was the next to stand up, giddy with excitement.

"Hey!" He greeted, adding a lame wave to his greeting. Serena let out a loud laugh, she couldn't help it. Nate looked so ridiculously awkward and so unlike Nate. So unlike this new power-hungry Nate she knew. For a moment he looked like _her _Natie. Innocent and fifteen, "Serena and Dan are two of my best friends and I love them both to bits and I'm so happy for them. They really are perfect for each other, they compliment each other perfectly and soon we'll all be family!" He joked, glancing at Jenny, the Vanderbit ring glistening on her finger, his eyes then skipped over too Dan and Serena lingering a moment longer then needed, "I've known Serena since I was four or five years old and while she's changed, she hasn't. You've matured so much - we all have - but you have still managed too be the happiest and brightest person I know. Dan, your one of the coolest guys I know and I'm glad your happy. I've only known you for what 11 years is it? But we've only grown closer and closer. I hope the two of you have a wonderful life together, filled with joy and happiness and everything you could of ever imagined. Thank you." Nate sat back down into his chair.

"Who's next?" He asked, glancing around the room.

* * *

Serena and Dan were dancing. The toasts had wrapped up around half an hour ago and everyone had only said positive things, excluding Chuck and Blair who mentioned to throw in something negative in their toast, and Serena and Dan couldn't be happier, they were on cloud nine. They rocked back and forth together, swaying in time to the music. It was peaceful and it was beautiful. And they were married, _husband and wife_.

"I couldn't be happier." Serena sighed with happiness. Dan couldn't agree more. He didn't know the last time he had felt this happy, he was with the girl he loved most in the world. He had always loved her, he had been blind to never see it before. All those other girls - they didn't mean a thing too him now - they were all just a distraction from Serena. Oh, _Serena!_ She was beautiful and kind and sweet and gentle and loving and perfect. She may of been his high school sweetheart but she was also now his wife.

"Me too." He replied, his voice laced with utter bliss.

"I can't believe it took us this long to get married." She sighed, half of her wishing they had tied the knot sooner. Eloped, maybe. She wished they hadn't spent so much time apart, with other people, figuring things out, not wanting to be together. She hoped that this time she and Dan really worked and deep down she knew they would, Chuck and Blair worked, hadn't they? And their relationship was complicated and messy.

"I know." Dan sighed, pulling Serena in for a kiss. Their mouths fused together eagerly.

"AUNTIE S! AUNTIE SERENA! AUNTIE RE!" Henry called out, trying out three different names to get his aunts attention. Serena reluctantly pulled away from Dan and faced the little boy. She scooped him up in her arms - he was too cute in his little bowtie - and he wrapped his arms around her neck.

"I want to dance with you." He explained, and so they did dance. With Henry way above the ground, and Serena spinning him around and the whole time she was with Henry she was thinking: _I want this, I want this with Dan. A little baby, that I can watch grow, and dance with and play with. I want this so badly._

* * *

Lily and Rufus had found each other after the speeches and had gone outside too have a drink, one drink had turned into two and two drinks turned into three and three drinks had managed to turn into ten or eleven and now they were very, _very_ drunk and were having too much fun. They had somehow stumbled up too one of the guest rooms in the Basses town house, in each others arms. Kissing and touching and tearing clothes of. They weren't thinking, both forgetting that downstairs their partners were waiting for them, too lost in their own world to use protection. Just too lost in each other.


	3. Honeymoon Woo's

**Title: **Heartbreakingly Perfect

**Summary: **Choices are made and hearts are broken. Paper gets crumpled up, mistakes can't be erased. Two paths cross and fireworks explode. People are messed with, people fire guns. Pull the trigger and I'm all yours. People forgive and forget, some hold grudges and try and get revenge. History is pulled up from the past and people are in _big _trouble. Post 6.1O.

**Authors Note: **Ahh! So I _finally _updated. I know! So enjoy this chapter, I was going to make it longer but I have homework to do and I wanted to get this out tonight. That's why the end seems like a weird place to end it.

**Disclaimer: **I own nothing as per usual.

* * *

**LOST IN YOUR EYES**

* * *

Jenny grinned at Nate from over her cup of coffee, he was staring intently at a newspaper - not a Spectator one, she noted - that had the words "Murder" splayed across the top. She shook her head at her boyfriend and tucked a stray piece of ear behind her ear, she picked up her cup and took a sip of coffee. She placed the cup back down on the table and picked up a slice of toast, ripping bits off of it and chewing it. She leaned over the table ever so slightly, itching to get a look at the paper. Nate didn't even glance at her, she let out a heavy sigh, hopping Nate would hear it and pay attention to her which he didn't. She fell back into her chair, planning her next move. Her eyes lit up as a plan came to mind, she grabbed the newspaper from off of the table and placed it in front of her. A scowl came to Nate's lips.

"Hey!" He exclaimed, reaching back for the paper. Jenny's eyes skimmed over the words as quick as they could before Nate had snatched it off of her. She frowned and fake pouted before reaching back for it, Nate held it up above him in the air, a grin applied to his lips. Jenny pushed her chair away and stood up, stretching slightly before pouncing on Nate and grabbing the paper. He pulled her onto his lap and she threw the paper into the corner of the room before attacking Nate's lips. His phone buzzed and he tore his lips away from hers, she sighed as he picked up his phone and answered the call, lightly pushing Jenny off of his lap.

"Can I call you back?" He asked, which brought a smile too Jenny's lips. Nate nodded his head and grumbled a miserable yes into his phone before hanging up and flinging it back onto the table. Nate then spun back around to face Jenny, an eyebrow raised.

"Where were we?" He asked and Jenny rolled her eyes because it was the corniest line she had ever heard but she flung herself into his arms anyway because she loved him, even if he was a complete and utter dork. Their lips met once again and they stumbled into the bedroom they shared. They fell back onto the bed and Jenny giggled. Nate grinned, she had changed so much, not really changed per say. He had noticed shortly after he had broken up with Sage, that she wasn't a raging queen bitch anymore but that sweet girl he had thought he liked in his Senior year of school and the girl he knew his Junior year of school. He pressed a kiss to her bare shoulder just as Jenny's phone went off, she sighed as she reached out to swipe it from off of the table. She looked at the caller ID quickly, her thumb hovering over the end call button and groaned. She flashed the phone towards Nate and hit answer call, holding it to her ear.

"Blair," She greeted, walking into another room to take the call. Nate covered his face with a pillow, yelling into it as he did so. Sometimes he really, _really_, hated Blair. Nate removed the pillow from off of his face to see Jenny walking back into the room again, her clothing all in perfect place. She shot him a small apologetic smile as she slings her bag over her shoulder, he stifles a groan as she walks swiftly over too him placing a small kiss on his lips. Her fingers grazing the curve of his cheek lightly.

"Bye." She whispers, his eyes shut close and a light smile comes to his lips at the sound of her voice.

"I love you," She shouts behind her back as she races out of their apartment, not wanting to be late to work. Blair would murder her in a heartbeat which would mean she would basically be left with no job and no chances at finding a job anywhere else. Jenny ran a hand through her hair as she stood on the curb of the street, hailing down a cab. She bit her lip, nervously jumping from foot too foot as cars raced past, no yellow and black in sight. She's already dead. 6 months into working for Blair Waldorf-Bass who has hated her since she was a freshman at high school and already she's screwed up, she takes a moment to check the time on her phone and nearly lets out a scream. She was meant to be at work exactly seven minutes ago, Blair does not appreciate _anyone_ being late for work, let alone Jenny. Finally she manages to hail a cab, she slips inside, chucks a twenty dollar bill at the driver and snaps for him to drive her to the Bass townhouse. Blair has requested a special meeting at her house, Jenny allows herself a moment to relax. She isn't going to be fired. She isn't going to be fired. She repeats the mantra in her head until she believes it or nearly believes it at least.

"We're here, Miss." She's out of the car so fast she swears she has super powers. Within seconds she's entering the townhouse, a nervous smile placed on her lips.

* * *

"We're married." Dan tells her, clinking his glass against hers. Serena throws her head back in laughter, her blonde hair that she curled this morning falling against her chair and tumbling over her sun kissed shoulders and Dan swears in that moment that's he's never seen something so beautiful. Her lips curve into a grin and her chest heaves with laughter, she throws her head back to it's normal place, her eyes shinning with glee and excitement. She clinks her own glass against Dan's and winks at him.

"We're married." She repeats, mimicking Dan. It's his turn to laugh but it's not nearly as graceful. His lips form a grin and his eyes twinkle with happiness because he _is_ happy. Serena makes him happy and all the foolish, _foolish_, mistakes of their past have been forgotten. Dan raises the glass of champagne to his lips, never taking his eyes off of his bride. Three days of being married and he's still unable to believe it. Three days of being married to Serena Van Der Woodsen. All his dreams from his youth have come true, he remembers keeping a notebook with a list of things he wished too achieve before the age of thirty and he's achieved fourteen out of fifteen of them. One of them being marrying Serena Van Der Woodsen. He takes a small sip of champagne and watches as Serena blushes under his gaze.

"Stop staring at me, _Humphrey_." She teases, brushing a strand of hair away that's fallen into her eye behind her ear. He shrugs his shoulders, ignoring her comment.

"I'm sorry _Mrs. Humphrey_," He jokes, a laugh escaping his lips. Serena pulls a face, disgust and distaste written all over her features. She shakes her head, the curls tumbling around her face.

"I'm not going by Mrs. Humphrey. I will keep my maiden name, I love you Dan _but_ your still a Humphrey." Serena may have the power to build him up and make him shine but she also has the power too cut him in half and make him feel like he's still that complete utter loser from Brooklyn. Her face softens as his grows harder, she reaches her hand out and places it on top of his. He doesn't pull away but he makes no attempt to grab her own hand and hold it in his own.

"Dan, I didn't mean to hurt your feelings but I want to be a Van Der Woodsen. My name is apart of me and everybody knows me by that name," She tries to explain, an encouraging smile taking home on his face. He pulls his hand away after this statement, pushing his chair backwards, letting it scrape against the floor.

"No, Serena. You don't want to carry my name around because I'm from _Brooklyn_." He spits before storming off into the resort they were staying at. Serena sits there, hands in her lap, her mouth forming a perfect "O" shape. She's never cared about where he came from but she's never carrying a man's last name. The only person's last name she could ever think about wanting as her own would have to be Nate's. _Archibald. Serena Archibald. _That's all she's ever wanted, all she ever _wanted_. She doesn't want it anymore but he's the only person she can think of to call, Blair would brush her off and tell her she shouldn't of married Dan to begin with, Chuck would listen but would end with she shouldn't of married a Humphrey to begin with but Nate would understand. He _will_ understand. She scrapes her own chair back and unclasps her clutch, her hands searching for her phone. Her fingers curl around it and pull it out. She hits speed dial #3 and holds it to her ear.

"Nate." She says, her voice cracking. Tears falling from her eyes in free-fall, a hand goes over her mouth. She's meant to be enjoying herself, having the time of her life not to be in tears on her honeymoon because her husband is upset that she won't take his last name.

* * *

Henry ran his hands along his train set, his eyes like that of a hawks, inspecting it for any damages. Blair giggles from her seat in Henry's room, her legs carelessly thrown over Chuck's lap. Henry spins around to face his parents upon hearing Blair's laugh, he crosses his arms against his chest and _pouts_. He actually pouts, stomping his feet on the ground.

"DO NOT LAUGH AT ME!" He exclaims, shrieking for the whole house too hear. He throws his arms up in the air to further his point and spins back around, going back to inspecting his train set. Usually Blair would scold him on his behaviour and demand that he apologize but she hears the door open up below her and a smirk crosses her lips. Her head lifts up too check the time on the clock and frowns. Jenny Humphrey is late. Very late. She sighs as she walks down the stairs, she doesn't rush of course. She walks down gracefully, her hand just above the handrail. A society smile in place, as soon as Jenny sees her employer she knows she's in trouble. Blair doesn't wear society smiles unless she's mad or at a society event.

"Jenny," She greets warmly. A little too warmly, Jenny notes. Jenny smiles at her but doesn't open her mouth. She knows better then to utter one word while she's in trouble. "You're late." Blair notes, her foot landing on the last step, her other foot quickly follows. She freezes, an eyebrow poised in the air, waiting patiently for Jenny's answer to why she's late. Jenny opens her mouth but no words come out, she feels as if it's even dangerous to _breath_ at a time like this.

"I was waiting for a cab and none came in time for me too arrive in time," She tells her nervously. Her fingers playing with the hem of her dress, Blair's eyes rake over her before her lips settle in a smile. She rolls her eyes and leads Jenny into the living room.

"Don't be so nervous, Little J. Believe it or not you're here for a promotion." Jenny stops in her tracks, her mouth hanging open. The words processing in her mind.

"A _promotion?_" She whispers, her voice laced with excitement and disbelief. Blair nods her head, she didn't want to give Jenny a promotion but her line had been doing so well and she needed to promote Jenny. She would feel like she was being unfair to Waldorf Designs if she didn't.

"Yes a promotion, as much as it pains me to give you one, you deserve it."


	4. Barcelona

**Title: **Heartbreakingly Perfect

**Summary: **Choices are made and hearts are broken. Paper gets crumpled up, mistakes can't be erased. Two paths cross and fireworks explode. People are messed with, people fire guns. Pull the trigger and I'm all yours. People forgive and forget, some hold grudges and try and get revenge. History is pulled up from the past and people are in _big _trouble. Post 6.1O.

**Authors Note: **Short chapter but it's something right? I updated the summary to something that might make people want to read this story btw. Also to the guest reviewer, this story isn't going to be a blissful one. It will be corny and it isn't a Dan\Serena fic. It does include snippets of them but it is not under any circumstances a DS story. This is heavy on Vanessa and includes a very important snippet of rufly at the end.

**Disclaimer: **I own nothing as per usual.

* * *

Jenny arrived home an hour after she left, a smile on her face that she couldn't wipe off. She looked like a complete and utter idiot but she didn't care, she had gotten a promotion! She tip toes through the house, opening the door to her and Nate's bedroom slightly and peeking inside. Nate's lying down on the bed, phone in his hand, laughing away. She slips inside, the smile falling from her face. Her eyes questioning and suspicious. He looks up at Jenny and beams, he points a finger up in the air. (One minute, Jen. I swear) She reads from his lips and eyes. She sits at the end of the bed, watching him carefully closely. It's probably Maxine from work, she's funny and makes anybody laugh.

"OK. Bye, Serena." And then he hangs up, her chest hurts, it tightens because Serena _Humphrey_ shouldn't be making her boyfriend laugh like that, she shouldn't be the one bringing the smile to his lips. Nate wraps his arms around Jenny's waist and pulls her in closer, she works a smile onto her face because she can't let him see that she's jealous and hurt.

* * *

"Barcelona!" Vanessa calls giggling, a champagne flute in one hand. She's running through the sand, her bare feet making prints in the soft grains. She's flinging herself on her boyfriend's back in a matter of seconds, she's a giggling mess and she's going to regret everything in the morning but she just wants to erase the pain of Dan marrying Serena right now. Barcelona simply chuckles and gently eases her off of his back, she _pouts._ She's not fucking Blair Waldorf or Serena Van Der Woodsen! She tugs on Barcelona's collar, pulling him closer towards her. His lips brush hers slightly and she leans in more, desperate for human contact. They stumble backwards and Barcelona catches her arms pulling her upright. He's wearing a frown and looks almost embarrassed by her. He hooks her arm into hers and they walk back to their apartment. Vanessa's long lost the champagne flute and her head is starting to clear up, just a little bit. Barcelona fumbles for a key in his pants pocket and pulls it out, jamming it into the key hole. The door flings open and the couple walk - _Vanessa stumbles_ - inside. Vanessa dives right for the bed, clawing her way up to the top and pushing the covers down with her feet. She shuts her eyes and orders the thoughts of Dan Humphrey to go away. She's with Barcelona and he's with _Serena_.

Plus he had betrayed everyone. He had been the anonymous blogger from their youth. The one that had tormented his friends and her. He had always tormented himself. Barcelona slides in next to her, stripped of his clothes. He throws an arm loosely on her stomach and she turns around, so he back is facing him. His arm winds itself around her waist and brings her in closer, pressing a series of kisses along her neck, jaw, cheek. A small groan exits Vanessa's lips because she wants Barcelona, she wants a life with him, she wants him but her thoughts are always leading towards Dan. She slides out of bed, shooting him a smile over her shoulder as she tip toes towards the bathroom. She shuts the door behind her and locks it, sliding down against it and putting her head in her hands. Her life was _never_ supposed to turn out like this, she was supposed to make it as an indie-film director and she wasn't meant to worry whether or not Dan Humphrey liked her and she _knew_ that he didn't but she still wanted him too even after everything, even while she's with Barcelona. She clutches her chest and breaths in and out a few times before lifting herself from up off of the ground and turning the tap on for the bath. She feels more sober then she has ever been, she strips away the few layers she has on and lowers herself into the bathtub. Her head ducks lower and lower down and then she floats back up again, swiping a bottle of bubbles from off of the floor. She pours it into the baths and waits for it to go bubbly, within seconds Barcelona is pounding on the door, asking if he can come in. Vanessa bites her lower lip and replies sure, he tries twisting the knob but it won't open.

"Vanessa, it's locked." He calls out and she breaths a sigh of relief, a smile over taking her face. She needs this time for herself,

"Oh. I would get up to unlock it but I don't want to get the floor wet." She lies, easily. Spending that much time on the Upper East Side has really payed off, she can now lie her way through anything. She shuts her eyes and sinks to the bottom of the tub. Barcelona is barging through the door not a minute later, proudly sporting a key in hand. He's wearing nothing, at all, but an anklet around his ankle. He hops into the bath and Vanessa tries her best too scoot over, once he's in, he pulls Vanessa onto her lap. He's growing erection pushing against her, she gulps and asks him shakily to pass her the shampoo bottle. She's on the verge of running out and breaking his heart, like she has been before. He passes her the bottle and she squeezes a dollop of shampoo onto her hand and she massages it through her head, resting her head against Barcelona's back. He finishes rubbing it into her scalp and through her long tresses. It's the moments like these that she realizes how much she truly loves Barcelona. Moments like these why she wonders why she still thinks about Dan, why she still misses him and there she goes again. She scoops up water in her hands and pours it over her hair, scrunching her eyes close. Barcelona joins in with helping her. He helps her for the rest of the evening, conditioner, body wash, shaving. Once she's done, Vanessa hops out of the water and wraps a towel around her body and another one around her head. She doesn't look back at Barcelona as she exits the bathroom and walks into their bedroom, fetching clothes for herself. Barcelona doesn't bother her until she's dressed, he's exiting the bathroom, an eyebrow perfectly arched and a towel loosely wrapped around his torso. Vanessa giggles at his pose, lips puckered and a kiss mid air and climbs into bed, pulling the covers up too her chin. Barcelona wiggles out of the towel and leaves it on the floor, crossing over to where Vanessa lays and climbing in next too her. She had almost forgotten that Barcelona liked to sleep in the nude.

"Night," Vanessa whispers her voice barely audible, a little lower then a whisper. She doubts Barcelona even heard her. She drifts off to sleep her mind betraying her with images and thoughts of Dan.

* * *

Lily stares down at the test in her hands, her breath caught in her throat. Her mind unable to find any words, unable to process any thoughts. She takes a deep breath and lets it out and then takes another and another and another, letting them all out. Her hand flies up too her chest and she clutches the fabric of her dress, not caring that she'll crinkle it. It's not possible, is it? She's pregnant. She's pregnant! And then it dawns on her, her and William hadn't slept together for me then three months but she and Rufus had. The test falls out of her hands and hits the ground with a soft thud. Her fingers reach out for her mobile on the counter, trembling. She's shaking. She swoops it up and searches for Rufus's number, she hits call and holds it up too her ear. She waits for him to answer and when she does, she can't find anything to say.

"I'm pregnant and I think it may be yours," The words tumble out of her mouth before she can stop them and she curses herself for being so stupid. She curses herself for cheating. She hears Rufus's breath halt on the other end of the line.

"Fuck, Lily," He breaths, his voice full of anger and pain. He hates her, he's mad at her. "It can't be possible." He tells her and oh, how she wishes he was right and he might be but she knows deep down that he's not.


	5. Haunting Pink Plus Signs

**Title: **Heartbreakingly Perfect

**Summary: **Choices are made and hearts are broken. Paper gets crumpled up, mistakes can't be erased. Two paths cross and fireworks explode. People are messed with, people fire guns. Pull the trigger and I'm all yours. People forgive and forget, some hold grudges and try and get revenge. History is pulled up from the past and people are in _big _trouble. Post 6.1O.

**Authors Note: **Another short update, I apologize! I wasn't going to include the end bit at first but then I thought I said probably make it a _little_ longer and we hadn't seen a lot of CB yet. _We_, I mean_ you_ if your reading. If you are could you please review? I hate asking for reviews but even if it's a dot, just so I know that I have readers, I would rather in depth reviews but beggers can't be choosers.

**Disclaimer: **I own nothing as per usual.

* * *

Serena sneaks into her and Dan's room later on in the night, it's some time after midnight, it's somewhere around five in the morning. Serena's not sure, she's lost track of the time while her head has been lost in the clouds, in the sky. She spots Dan's sleeping figure, curled up into a fetal position, the covers loosely thrown around him and Serena's heart breaks because she made the wrong choice in marrying him. She loves him, she really and truly does but he's her _highschool boyfriend_ and nobody is supposed to end up with the person they loved when they were sixteen. She quietly removes her heels and throws them in the corner of the room, they land with a soft thud. She undoes the zip of her dress, letting it slide down her body. It puddles at her feet in the floor and she steps out of it, she makes her way towards the bed and throws back the covers, sliding in next to Dan. He grumbles slightly but he doesn't stir anymore. Serena's eyes flutter close and soon enough the darkness has taken her as a victim. She awakes some time in the late afternoon, the sun's blinding when she opens her eyes and Dan's sitting at a desk in the room, a pen in hand hovering over the desk where a notepad lies. His eyes are focused in on the notebook and his teeth are sinking into his lower lip in concentration. Serena flings the covers off of her body and pads over towards Dan. She rests her hands on his shoulders, startling him. He whips his head around and a light smile is brought to his lips when he spots Serena. She returns the smile and places a light, dainty kiss on his cheek. He pushes the chair away and flings his arms around Serena's neck, bringing her in closer.

"I'm _so_ sorry." Dan apologizes, laying a series of kisses along Serena's collar line. She closes her eyes and lets herself get lost in Dan for a second but she has to break it off with him or at least attempt to work it out. She doesn't want a divorce, she doesn't want to end up like her mother but she thought if she and Dan got married all their problems would just vanish but last night was proof that if Serena does something Dan doesn't like, doesn't want, he'll take it out on her. While it's not always true, she has done it quite a few times herself, she and Dan can never solve their problems they only create more. She peels her eyes open and takes a step back, Dan takes a step forward, his arms still attached to Serena. She takes them off of her neck and lets them fall limply at his side. His mouth contorts into a frown, his eyes questioning. She takes another step back, she takes a deep breath in and lets it out.

"Dan," She starts, a hand running through her blonde locks. She stares down at the ground, unable to face Dan. He knows what she wants to say, what she _has_ to say and he doesn't want to hear it. "I love you." She mutters, unable to find it in her heart to break the news to him that they need to work on their relationship. Dan doesn't take it, doesn't believe her but a smile of relief washes over his face anyway. Serena flings her arms back over his neck, pulling his face closer to hers. Their lips crashing together, tongues twisting in a fiery dance. Dan's the first to pull away, his eyes shooting back towards where his notebook lay.

"I was sort of working before you woke up." He mumbles, Serena nods her head in understanding. Trying to ignore the feeling of rejection.

"Oh. Right, of course. Get back to work, I was thinking about checking out the shops anyway." She lies. She hadn't even thought of the shops, a first for Serena Van Der Woodsen. Dan smiles in relief for the second time that afternoon and he returns to his chair, returning to his previous state of affair. Serena walks towards the door, twisting it open and sending one last look Dan's way. She has one foot out the door when she remembers what she's wearing and she almost gasps in shock. It's not unusual for Serena to be seen in just her underwear but she's a grown up now, she's married now and she's going to try her hardest to act like a married grown up. She picks a dress out of the closet and slips into it, placing a hat upon her head and her feet into floral wedges. She slings a bag across her shoulder and then she's gone, out into the busy streets and the chaos. Her eyes scan clothing racks and shoes but her mind is to busy focusing on her boy drama to register any of the beautiful silk and satin. _Boy drama_. She's not a child anymore yet she still has boy trouble. She whips out her phone and dials a number that she had used last night,

"Nate." She breaths when he answers, a smile lighting up on her face.

* * *

Rufus stares down at the test lying on the bathroom sink, Lily's standing next to him furiously biting her nails. A bad habit from her teenage years that _always_ comes back when something major happens in her life. Rufus sighs angrily. There was no way in hell that the child Lily Van Der Woodsen was carrying was his offspring. They had been there, done that. Neither are saying anything, they can't think of any words to say. Rufus shoots a glance at Lily but she doesn't notice, she's to busy staring at the test herself. He had come over straight after the phone call, forgetting all about the time and the fact that Lily was married and he had a girlfriend. William was away on some trip and Rufus had made up some simple lie to tell Lisa. _A lie_. He had lied to his girlfriend about visiting his ex-wife who may or may not be pregnant with his child.

"It could be faulty." Rufus offers at last. Lily looks up at him, a hopeful expression lights up her face. She'll grasp at anything for this not to be true even though deep down she knows it's not faulty. She knows it's not a fake. The smile drops right off of her lips as she marches towards the sink, she pulls out another pregnancy test and shoots Rufus a pointed look. His face dawns with realization and he shuffles out of the bathroom, closing the door quietly behind him. Lily lets out a breath and prepares herself to take another test.

Three minutes later two eager eyes are staring down at the test, hoping and praying that it'll come up negative but their hopes and dreams are crushed when the little pink plus sign appears. Lily takes three more tests and they all come up positive. Rufus's hands are curled up into fists by this point. His eyes seething with anger and Lily looks like she might faint.

"There might be a chance it's not mine right?" Rufus asks and while he says it, he doesn't want it to be true. He wants to be the only one to father Lily's children even if two of her children are from the man she's married to right now but then on the other hand he doesn't want to be the father. He has a girlfriend whom he loves very much and their children are married. _Married!_ For god's sake. This couldn't be happening but it was. Lily shook her head, biting her lip. Her eyes were downcast towards the floor.

"William and I, we haven't, we don't." She searches for the right words but Rufus's nod saves her. He knows what she means which also means that the two of them are going to be having a baby together. Lily sighs and falls into Rufus's arms. Her life was like some stupid reality TV drama in which everything went wrong and they were utter fools. They _were_ utter fools and there was only one thing Lily could think about doing. She pulls away as she starts speaking.

"I need to book an appointment with my doctor. I'll schedule an abortion." The words tumble out of her mouth, her mind racing. Rufus's jaw drops to the floor. An abortion?

"You can't abort this child, Lily!" He all but screeches, anger rising within him. She's mid way through pulling her phone out when she looks up at him. She sighs and shakes her head, her bun coming loose.

"Rufus. You don't understand. It's the only way." She tries to explain, she can't lose everything for a child she doesn't want. She prides herself on being a mother but she doesn't want to give birth to a child that she doesn't love right away. She had loved Scott with everything she had when she found out she was pregnant with him despite being scared, she had loved Serena with everything she had when she found out she was having her and same went for Eric and then as soon as she started seeing Bart, she had started loving Charles and yet, now, she's having another baby and she doesn't love it. She can't have it, what would happen to her and William? Rufus and Lisa?

"No. Lily, we'll work through it. Alright." He tells her. She _almost_ believes him. She wants to believe him and so she nods her head and puts her phone away. She wouldn't speak any more of the subject, she could pretend to be having the child and schedule an abortion secretly, tell Rufus it _was_ a false alarm or a miscarriage. Either wouldn't work though, Rufus wouldn't believe her. He sees right through her.

"What are we going to do?" She whispers, her voice breaking. Rufus shakes his head and shrugs his shoulders, he has no idea.

"I don't know, Lil."

* * *

"And my teacher said I was very smart for my age." Henry finishes with a triumphant smile, he had been so excited to tell his parents all about what Miss Thomas had told him today at Kindergarten. He had been excelling in his school work, he knew all his ABC's and could write a few sentences and he knew how to count up to twenty already. Blair smiled and pulled her son onto her lap, Chuck put his hand up into the air for Henry too hi-five.

"Good work, Hen." Chuck told him genuinely, he couldn't be any more proud then he was at the moment. Blair kissed the top of her sons head and congratulated him in a whisper so only he could hear the kind words, a secret between them. Henry hoped off of his lap once she was finished and ran towards his bed. Both brunettes stood up, getting ready to tuck their son in.


	6. Surprise!

**Title: **Heartbreakingly Perfect

**Summary: **Choices are made and hearts are broken. Paper gets crumpled up, mistakes can't be erased. Two paths cross and fireworks explode. People are messed with, people fire guns. Pull the trigger and I'm all yours. People forgive and forget, some hold grudges and try and get revenge. History is pulled up from the past and people are in _big _trouble. Post 6.1O.

**Authors Note: **This is the shortest thing ever and I don't like the ending. This was rushed but I really wanted to post another chapter, I was actually going to make this a lot longer but instead I cut it all up. I haven't actually written anything. Reviews are appreciated!

**Disclaimer: **I own nothing

* * *

"Serena, if you don't want to be married to Dan anymore you have to tell him." Nate sighs, he's been on the phone with Serena for an hour or two, he's lost track of time and while he's always happy to help her out _and_ hear her voice, he doesn't think he can listen to her droning on about making the "wrong choice".

"But Nate, I don't _want_ a divorce and I still love Dan." She states, he can imagine her pouting on the other line, flicking through racks of dresses and rambling on in a store where everyone's staring at her because she's beautiful and what she's saying makes no sense at times. A light chuckle escapes Nate's lips as he clicks on the Spectator website on his laptop, going to the editor page.

"What do you want then?" He asks and her voice halts on the other line. She doesn't know what she wants, she always wants something one minute and something new the next. His fingers move away from the keyboard and he leans back in his chair, waiting for her answer.

"I don't know what I want, Nate. _That's_ the problem!" She wails on the other end. His heart breaks because it sounds like she's on the verge of tears and nobody can help her but him. She didn't go to Dan, she didn't go to Blair, she didn't go to her mother, or Erik, or Chuck. She went to him. Her rubs the bridge of his nose, he can feel a bad headache coming on and slides out of his chair to pace around the room.

"Come home then," He tells her, picking up some files off of his desk and skimming through them, "Come home and we can talk face to face and I can help you talk to Dan." She pauses once again before mumbling a yes and hanging up. This wasn't what a honeymoon was supposed to be like, Dan working, her rethinking her choices. Just how did everything get so screwed up? She slumps against the changing room door she's in and dials Dan, she has to do this now. Not later but now. He answers on the fourth ring.

"Serena?" He answers with, he sounds tired. She bites her lower lip, maybe she should call back later? No, she has to do this now.

"Dan!" She replies, her voice too over the top and sugary sweet. She cringes at the sound of it but Dan falls for it, he doesn't ask any questions. He just remains silent, she called him, remember?

"Dan, I think we should go back to New York." She quickly spits out, like ripping off a band aid. Quick and painless.

"What? Why?" He asks, his voice panicky. He knew it, he just knew it. This morning something was off, she was going to break up with him or something. Wasn't she?

"I miss Henry too much," It wasn't a lie. She did miss Henry but not so much to go home. Dan sighs on the other end.

"Fine." He responds sharply before hanging up. The phone falls limp out of her hand and hits the wooden floor with a soft thud. She squeezes her eyes shut, trying to get rid of the tears but it's no use. They fall anyway and she chokes on them, drowns on them. It's not fair, this isn't what marriage is supposed to be. This isn't what her honeymoon should be like, her and Dan should be exploring each other's bodies not fighting. Not _silently _fighting. Serena doesn't bother moving, she makes no effort. What's the point anyway? She doesn't have anything anymore, she's becoming her mother. She can herself in ten years time, onto her third husband. A quick fleeting romance that would end in a divorce. Children to different suitors, and she would always be travelling. A choked cry escapes her lips because it isn't fair. She's never found herself having to work for anything but she knows she has too work for _this_, for her and Dan. Otherwise it could be over for good, she could lose him. She pushes herself up off of the floor and waltzes out of the shop, her cheeks are stained with mascara and her eyes are blury with tears but she feels confident somehow because she knows what she has to do and it isn't ending her marriage, it's saving it.

* * *

Blair sighs as she hears her best friend rambling on the other end of the phone, she sounds slightly drunk and she's in one of those moods where she believes she can change everything with a snap of her fingers, which she can because she's Serena freaking Van Der Woodsen. She's also talking so fast, Blair can't get a word in nor can she even understand what she's saying. She does however catch one phrase _"I'm coming home, Dan and I are coming home. We'll see you tomorrow." _and then Serena's hanging up on her and Blair doesn't have any time to tell her to stop, to wait. She turns around to face Chuck, he's flicking through the channels on TV, Blair's teeth bite into her lower lip as she climbs into bed next to him, he turns his attention to her and presses a kiss to the side of her forehead as she snuggles up closer to him, throwing a leg over one of his.

"How's my favorite sister?" Chuck asks, his eyes trained on the stock market. Blair rolls her eyes and scoffs, picking up the remote and changing it to the classics channel, getting a little giddy as Sabrina's opening sequence flashes on screen.

"She's coming home with Dan." Blair states, her eyes watching the screens every move. Chuck lets out a small chuckle, changing the TV back to the stock market. Blair pouts and reaches for the remote but Chuck's held it up out of her reach, she whines his name but he shakes his head.

"You've seen Sabrina, how many times? Why would S want to come home anyway? She's on her honeymoon, not that I approve of her choice of husband." Blair tears the remote out of Chuck's hand and puts it back onto Sabrina, tossing the remote to the other side of the room way out of Chuck's reach. Blair shakes her head, her loose curls tumbling down her front.

"Who knows what goes in that head of hers?" Blair scoffs, a hint of annoyance in her voice. When Serena's finally settled down, it seems like more drama's about to erupt and Blair has a feeling the only reason her best friend is coming home is because she isn't happy with Dan, who could be truly happy with a brooklynite? But Blair does hope that she isn't right, she wants Serena to be happy and she wants her to be stable.

"When is she arriving? I was sort of looking forward to time without your blonde sidekick." Chuck jokes, drawing circles with his fingers on Blair's arm. She shivers under his touch, even after all these years and directs her attention on the movie. Chuck however has other things on his mind as he gently nips at the skin on her neck.

"Chuuuck." She whines, doing her best to push him off of her, its to no use though. He's only gone and wrapped his arms around her and he's doing his best to pull her closer, to turn her around. She whips her head around to face him and presses her mouth into his, their tongues lapping at one another. Blair's hands are traveling through his hair, getting wound in his brown locks. Blair's sitting on his lap, her legs wrapped around his back and then Henry barges in. A small gasp echoes from his mouth but it's hardly the worst thing he's ever walked in on, Blair quickly untangles herself from her husband and rushes to her son's side, shooting Chuck a glare. He shrugs his shoulders, it's not _his_ fault that their son walked in on them. Henry's hands reach up for Blair and she swoops him up into her arms, planting a kiss on the top of his head.

"What's wrong, sweetie?" He should be in bed right now, sleeping peacefully. His lower lip trembles and he looks away, his hands reaching up for Chuck to take him. Blair passes him over and Henry wraps his legs around his father's waist, resting his head in the crook of his neck.

"I had a bad dream," He finally tells them, his eyes blurry with tears. Blair's heart breaks and Chuck sits back down on the bed, Henry still in his arms. He smooths back his son's hair.

"Do you want to tell us about it?" Chuck asks softly. Henry shakes his head and clutches onto his dad tighter. He doesn't want to think about it, it was too horrific, too violent, to _dreadful._

"Auntie Serena's coming home tomorrow." Blair offers, in a lame attempt to cheer Henry up but it works because the mere mention of either his aunt or uncle has him beaming like it's Christmas and his birthday and Easter combined. Chuck rolls his eyes at his son, he'll never understand why his day is always made better at the mention of Serena. She isn't anything special, Chuck has a feeling Henry only likes his aunt and uncle because he's smarter then them. Not that Chuck would ever voice that thought out loud, of course. Henry's smile soon turns into a frown,

"But why? She's away with Dan." Blair nods her head and moves Henry over so he's sitting in her lap, her fingers stroke through his hair, she absentmindedly thinks about how he needs another haircut.

"They've decided to come back early, hun." She tells him, rocking him in her arms. Henry lets out a small sigh and crawls out of his mothers arms and tucks himself into his parents bed, a mischievous grin spreading across his face, Chuck shoots his son a small glare he does not want him sleeping in their bed. He's too old for that.

"Daddy, you have to let me stay. I walked in on you and mummy." Henry points out, Chuck groans and flops himself backwards onto the bed. The three of them had a rule, if Henry was ever to walk in on him and Blair he could have one "wish" come true for him. Blair giggles, apologizes to her son for letting horrific images flash before his eyes and slide in next to him. Chuck is quick to follow suit, nudging Henry over slightly so he could fit.

* * *

A Christian Louboutin clad foot lands on the ground, a wide smile plastered to the owner of the shoes face, her blonde hair swishing around her face as she slides her sunglasses up to her head. Her hand is enclosed in anothers, a male others who's not wearing a radiant smile but instead is sporting a grumpy frown. The blonde tugs on his hand as they fly down the busy new york street like they own the place, the female's long legs catching every male eye and nearly every females.

"Come on!" She exclaims, her legs picking up speed as she tugs on her partners arm. Dan lets a laugh escape his lips at the sign of _his_ wife. People stop and stare at the two but for the first time Dan doesn't care. Serena's knocking on the Bass's townhouse within minutes, shouting out for either Blair or Chuck and even Henry. Henry is the one who flings open the door and Serena scoops him up in her arms and plants kisses all over his face and tells him how much she loves him and how much she missed him. Dan shakes his head, pats Henry on the back awkwardly and lets himself inside.

"S!" Blair screams when she sees her best friend, she's decided to push all thoughts about the disapproval of Serena's sudden return to the back of her mind as she hugs her best friend.

"Sis." Chuck drawls as he greets her, Serena simply grins at the people around her, she's finally home.


	7. Big News

**Title: **Heartbreakingly Perfect

**Summary: **We were left watching a Humphrey wed a Van Der Woodsen, not knowing what would become of everyone's fate. "I lost my baby," She cries, her cheeks stained with tears. Post 6.1O. Pairings inside.

**Authors Note: **I apologize because this isn't a proper update. It is mainly Rufus\Lily but it does affect others. It's _very_, _very_, _very_ short but I wanted to update this as a single chapter. I'm really, truly sorry though and I will have a new proper update up in a few days and hopefully it'll be a lot longer, however it may be updated sooner if I receive more then ten reviews.

**Disclaimer: **I own nothing.

* * *

"How do you want to do this?" Rufus asks his former flame. Lily stops in her place, shoots him a glare and then goes back to pacing around the room. After both of them more or less agreeing that Rufus was the only candidate of being Lily's unborn child's father the two of them had decided together to tell everyone and with the arrival of Serena and Dan the timing was more then perfect. Lily took in a deep breath and then turned to face Rufus.

"We should do it like were ripping off a band aid," She finally breathed, pining the last of her hair up into a bun. Rufus nodded his head and stood up, absentmindedly straightening his shirt. Everybody was waiting out in the living room of the Van Der Woodsen Penthouse and all were curious as to why Lily had all called them there and then dragged Rufus in a room upstairs. The two of them began to descend down the stairs and with each and every step they took the two of them began more nervous.

They reach the bottom step and share a single look, an unspoken agreement for Lily to do the talking. She's always been the better talker, a graceful and very fake smile is placed on her lips as her eyes look around the room, how many people will lash out with her once the news is told?

"I'm having a baby," She pauses for half a second, taking in a deep breath, she doesn't have time to look at everybody's reaction, "I'm having a baby with Rufus,"

It's like world war three has began, William stares at her with a mix of anger and confusion, Lisa's screaming something at Rufus that sounds a lot like "I knew it, I knew it," and she's leaving the Penthouse, Serena's staring at her mouth her face a mixture of hurt, sadness and anger and Lily feels crushed. Dan's frozen in his place, a string of swear words ready on his lips. The two of them had to be fucking kidding.

"You can't be serious?" Serena spewed, her relationship with Dan already felt like it was on the edge she didn't need her mother having an affair with his father on top of it and it wasn't just an affair this time, they were having a child! Her eyes flashed over to her father who looked majorly pissed off and Serena couldn't blame him. She was angry at her mother as well.

"Congratulations," Chuck's voice said, a smile smile gracing his lips. Henry's standing next too him and Serena watches as everything processes in his brain, his mouth drops into a small "O" and he starts jumping up and down, clapping his hands.

"Does this mean I'm going to have a new aunt or uncle?" He asks excitedly, Blair rolls her eyes at her son and gently picks him up balancing him on her hips. The Bass family says a small farewell before they leave the scene entirely, they don't want to be in the middle of such a messy affair that doesn't directly concern them.

"Look, I know none of you are happy-" The look on William's face silences Lily and her eyes are cast downwards as she waits for his speech to take place.

"We aren't happy? Of course we aren't happy, Lil! You've slept with your ex husband while the two of us are married, while our child and his child are married and now you're going to have his child? We are over, Lillian." She feels as if she has been slap, each word stings her and marks her with red, burning marks in her heart. Her eyes flicker over to Rufus, he's been silent this entire time. His eyes are focused intently on Rufus, she knows he's trying to avoid Dan's harsh gaze.

"Dad, how could you?" Dan's voice echoes around the room, his grip on Serena's hand tightening. He must be dreaming, he has to be dreaming. He and Serena already share a sibling, they can't share another. Rufus hangs his head, his eyes watching his shoes like they are the most interesting thing in the world. He can't face him, it's to hard for him.

"When did _this_ happen?" Serena asks, gesturing to Lily and Rufus. Lily sinks her teeth into her lower lip, she doesn't want to tell them. They'll hate her, _them_, even more. Erik who has been silent up until now, stands up and walks back to his room, slamming the door behind him. Lily lets out a sigh, she knew this wouldn't be easy but she thought this would be easier then _this_.

"Your wedding," Rufus chokes out, Lily's eyes flutter shut because she doesn't want to see the look of pain and hurt flash across the children's faces.


	8. Wonderful Mistakes

**Title: **Heartbreakingly Perfect.

**Summary: **We were left watching a Humphrey wed a Van Der Woodsen, not knowing what would become of everyone's fate. "I lost my baby," She cries, her cheeks stained with tears. Post 6.1O. Pairings inside.

**Authors Note: **I want to start by saying sorry to those who actually read this, I've been awful! I just, I'm lost for ideas honestly. The lack of reviews haven't helped either. Please, please, review! I hate asking for reviews but it gives me inspiration, you know? If you have any ideas please post them because I have been suffering through severe writers block. This is about a months time jump from the last chapter.

**Disclaimer: **I own nothing.

* * *

Time had passed by within seconds it had seemed, Nate's body was pressed up against Serena's and he was planting a trail of kisses on her neck down to the base of her throat. Her hands were gripping at his hair, his shirt lay rumpled on the floor and her dress was crinkled beyond repair.

"I love you," He breaths against her neck and she's repeating the words back to him because she loves him. She loves him so much it consumes her. She's always loved him, ever since she walked into Kindergarten and he was sitting on the floor, his blonde hair rumpled and his blue eyes shiny. He had been playing with lego, making a plane or something and she had sat down next to him with a grin on her face that had made him fall in love with her at the very first sight.

The two of them have somehow found their way to the bed and it's all happening so fast, kisses are being planted _everywhere_ and screams are echoing through out the room and they somehow manage to forget their own names and for the first time in a long time the two of them are _happy_ and the only words they can remember are "I love you," and "Oh my god," and "Nate!" and "Oh god, Serena!" and everything seems so perfect.

But everything perfect comes to an end and eventually they come down from their high, the breathing stills and the warmth of the others body makes them feel safe. Nate's arm wraps around her waist as Serena turns her back on Nate and he scoots up closer towards her, her eyes are on the rings that adorn her finger and she's blinking back tears and moving out of the bed so fast, at a lightening fast speed. She's picking up her crinkled dress and her other articles of clothing laying on the floor.

"What are you doing?" Nate asks, getting up out of bed. She doesn't look at him, she ignores him as she slips on her dress. He's pacing back and forth and muttering about how it was too good to be true and Serena's bursting into tears and falling into a mess on the floor and screaming that she's sorry and everything has turned into utter chaos within a matter of minutes.

"Don't leave," Nate begs, grabbing her arm as her hand reaches out for the doorknob. She yanks it out of his grip and shakes her head, this was a mistake. A big mistake.

"I'm married! You're engaged!" She shouts at him, she doesn't care if anybody hears her. She's going to have to go tell Dan and Jenny, she _has _too but oh god, she doesn't want too. It will ruin everything and things are already rocky with her and Dan. She can't think straight, everything's been such a big jumble of words and feelings. Nate's taken a step back and he's pulling on his pants and buttoning up his shirt and he can't even remember how this happened. They were supposed to be babysitting Henry _not _getting caught up in past feelings.

"It doesn't change how I feel about you," Nate hears himself whisper but Serena's already out the door, her blonde hair flowing behind her and her long golden legs galloping ahead. She's like a goddess out of those mythical books there teacher used to read to them in year three, he remembers watching Serena as they story unfolded, her big blue eyes growing wider and wider, her perfect pout pink mouth agape. She would clap and cheer at her favourite parts, and cry at the saddest. He faintly remembers wiping all the tears away from her eyes after one of her favourite mythical gods or goddess's had died, he had held her close and whispered things into her ear that seemed to take away all of her pain.

He stands there, stupidly, watching the space where she had fluttered past. He's wearing nothing but un zipped pants and a shirt that's buttoned up in all the wrong places. Henry walks past, rubbing his eyes and dressed in silk purple pajama's with tiny grey elephants printed on them, it brings a small grin to Nate's face. Henry peers into the bedroom and crinkles his nose, he adds a small shake of his head,

"They're gonna be mad at you, Uncle Natie. You shouldn't be making a mess." He states before walking off and Nate seriously wonders how in the world Henry's smarter then he is - he hadn't even thought about Chuck and Blair yet. They would be _pissed. _He quickly shuts the door closed and sits back on the wrecked bed, swooping up his socks and shoes. First step was to get dressed. the next was - He paused, scooping up a pad of paper and a pen from off of the bedside table.

* * *

1. Get dressed.

2. Clean room.

3. Order chocolates for Serena.

4. Order flowers for Serena.

5. Break up with Jenny (crossed out, now.)

6. Tell Blair & Chuck.

7. Replace broken furniture.

* * *

He places the list on the side, carefully and tries his best to complete task one and two before Chuck and Blair arrive home, which he surprisingly manages to do. He glances at the list once more before Chuck and Blair barge into the room, he might replace 3 & 4 with 6.

"How was Henry?" Blair asks, eyebrow poised in the air, a hand on the hip. He gulps, he's _terrified _of her. He nods his head and gives a small shrug of his shoulders.

"Behaved perfectly well," Lies. He hardly saw Henry at all this evening but he _assumes_ that he behaved perfectly well, Henry always behaves perfectly well. A cruel laugh emits out of Blair's mouth and Nate cringes. Uh-oh, she's caught him out on his lie already.

"Then explain the mess in the kitchen, downstairs." She orders, Nate sighs already giving up.

"Look, I'll admit it, I was a little too pre-occupied. Um, something may of happened with Serena," He trails off nervously, Blair simply rolls her eyes and Chuck lets out a small chuckle.

"Seriously Nate? You're _fucking_ engaged and Serena's _married_. As much as Chuck & I adore the two of you together it's wrong, very, very, _very _wrong!" Blair hisses, shaking her head and throwing her hands up dramatically in the air.

"Did our golden girl do a runner?" Chuck asks, looking around the room - it's clean by Nate's standards but terribly messy by the Basses and there seems to be a tiny tear stuck in his best friend's eye. Nate nods his head and flops down onto the bed, his eyes look up at the ceiling.

"Yeah, again. She just left, it was, it was crazy." He mutters, blinking back tears that are bound to over flow.

"You have to tell Jenny." Blair orders, the name rolling off of her lips with as less disgust as she can muster. She still hates that brooklynite but not as much as she used too, Nate shakes his head.

"Not until I figure out where Serena stands. Where Serena & I stand." He tells them firmly before quickly leaving their townhouse. His destination? The penthouse she and Dan had just brought _together_. His stomach is twisting and turning and his mind is telling him this is a bad idea but his hearts telling him that Serena's _the one_, he's never loved anyone like he's loved her. His fist is pounding on the door of the master bedroom and -

"Nate?" Dan asks, surprise evident in his voice. Serena hovers in the doorway, a white fluffy robe covering her body shoulders to ankles.

"Dan," Nate greets, stepping foot into their home, his eyes inspect the bedroom and he wishes that he hadn't intruded _at all_. His eyes fall to the floor and he mutters his apologies before running out, he stabs the elevator button a million times before it finally opens and lets him inside. Once the doors have closed he slumps onto the ground and tries to catch his breathing. It meant _nothing_ Nate, _nothing_. He pulls out his phone and dials Jenny's number.

"Jen!" He greets, grinning when he hears her honey sweet voice on the other end. She sounds stress, Blair's been having her work later hours and earlier mornings. He hardly ever sees her anymore, he blames that reason on why he slept with Serena. "I've missed you, can you stop working and grab dinner?" He asks hopefully, smiling like a maniac when she says she can.

* * *

**A\N: Ok, so not a long chapter, at all. I was trying to write something longer but oh well, I wanted this to be mainly Serena\Nate focus and so I cut out some Nate\Jenny bits and some Vanessa\Barcelona and Vanessa bits. I also wrote a scene with Blair\Chuck\Henry after Nate had left but scratched it. I don't like this chapter, it's fast paced in the thoughts and actions and while I write it like that, I find it a bit messy and another **_**long **_**A\N. Reviews = love, love, love! **

**P.S: I understand that I totally didn't regard anything that had happened in previous chapters. I will explain what has happened. **


	9. Five Hours Earlier

**Title: **Heartbreakingly Perfect.

**Summary: **-

**Authors Note: **Thank you for the reviews. I totally understand where everyone is coming from, Serena and Nate are based a little more on their book versions - irrational, ditzy, not good at making choices multiplied by 100. I will come to explain _how _Nate and Serena ended up sleeping together in this chapter. The five hours earlier bit is set five hours earlier to where the last chapter ended.

**Guest: **Serena and Nate are a bit OOC and they're also based more on book!Nate & Serena, however your second reason doesn't really hold much ground as I see Serena throwing it away for anything and while they worked hard to be together, Serena's fickle. She changes her mind too often, reason one makes sense but at times you get the sense that Nate never really stopped loving Serena. The third reason is where it becomes major OOC, because Nate wouldn't betray his friends, not now. He would of in previous seasons but not now but thanks for the review!

**TheBithIsBack: **Oh I agree - my fics are depressing, utterly depressing but the amount of people who read depressing stories are large but the thing is people will follow it that won't review or people will fave it who won't review and does it really take so long to review? But thank you for your review and I'll keep it in mind but I doubt I'll be able to write something happy, what happy stuff I do write it just isn't _good_ at all.

**Guest: **Thank you so much for your feedback! It means _so _much.

**Disclaimer: **I own nothing, if I did I wouldn't announce it either because Gossip Girl died a _long _time ago. I'm just here trying to make it into a even bigger mess.

* * *

**Five Hours Earlier. **

"I can't believe that Blair and Chuck actually _agreed _for us to be in charge of Henry without Dorota. I think the both of them have lost their mind," Serena jokes, bringing the glass of champagne up to her lips. A small amount spills onto her dress, a tiny splotch but it's enough to turn Nate into having a fit of giggles. She smacks him lightly across the chest, her mind flitting back to memories of them as stupid children where the both of them would laugh at anything and everything, Blair and Chuck rolling their eyes at the two of them and would go back to talking about one of their latest schemes.

"You're so easily amused, Nate. I worry about you sometimes," She joked, her eyes fluttering closed and her arms stretching out behind her. Henry chose that moment to come bouncing into the room, mischievous grin wide across his face, his body clothed in silk purple pajama's small grey elephants printed on them, his hair sticking up at weird angles. Nate smiled at his godson, his arms opening up for Henry to run into. His tiny bare feet ran across the glossy hardwood floor and jumped into Nate's arms, he buries his head in the crook of his Uncle's neck and lets out a small content sigh.

"Love you, Uncle Nate." He whispers quietly, a yawn escaping his mouth. Nate's hand flies to the boy's back and rubs circles on the soft silk. Serena's eyes open wide and she watches one of her best friends and the product of her other best friend's love. She used to imagine that her and Dan would have _this_, a son of their own, a happy family but that had been shot to hell as the news of her mother's pregnancy to Rufus had been announced around a month ago, ever since then Dan had been distant, different.

"No love for your _favourite_ Auntie?" She squeals, attacking the little boy with her fingers, tickling underneath his armpits, his sides, his stomach, his little feet. He laughs and squeals and protests and it reminds them both of a younger Blair. His hands are flying around all over the place, smacking everything and anything, the air, his godparent's faces at one point. He's grinning like a madman and Nate comments that he would make a _perfect_ sideshow Bob. Serena lets out a golden laugh, memories of watching endless _Simpsons _re-runs floating through her mind, popcorn by the NJBC's side. Blair had scrunched her nose up at the poor humour as she called it but would be enthralled by it all nonetheless.

"No, no, no more!" The little one screams, shrieks but the laughter in his voice tells everyone that he doesn't really want this too stop. Nate and Serena eventually grow tired and Henry dozes off. Serena swoops the feather light child into her arms and carries him upstairs, Nate hot on her heels, trailing behind like a poor lost puppy dog. Nate peels back the sheets on Henry's bed and Serena slips him inside of the bundle of blankets, they both press kisses on his cheeks before closing the door to his bedroom and retreating back downstairs to the living room.

"Dan and I won't ever be able to have what Chuck and Blair have," She murmurs, Nate almost doesn't hear it but he does. He stops in his tracks, his hand slowly coming off of the rail as one foot lands on the floor.

"What do you mean? You and Dan seem," He trails off, searching for the right word, "_perfect_." He states, his eyes looking up at the ceiling before falling back onto Serena. She shrugs her shoulders and he can see the glistening tears in her pretty blue eyes that shine bright like diamonds. Her lower lip is quivering.

"God, everything's so screwed up Nate," She finally says, her voice rising higher and higher with every word before falling back onto a hushed whisper with his name. She bites her lower lip, a small amount of blood spilling out onto her peach lips. Nate's moving towards her quicker and quicker, his arms wrapping around her shaken form. He doesn't think he's ever seen Serena look this weak and he's spent a lot of time looking at her, looking at a weak, lost girl. He remembers the times where she used to come home drunk, peppering his face with kisses and singing some stupid song. When she used to snort cocaine until she forgot her own name, wandering the streets of New York until it was four in the morning before landing on his doorstep crying her eyes out.

"Fuck. Nate, I, I want everything to go back to the way it was, _before_." She whispers, her eyes dropping to the floor, small tears slipping onto her face. His heart hurts because it's been so long since he's seen Serena like _this_, lost, confused, sad. Her body trembles with sobs, she loves Dan. Loves him more than she loves herself, more then she loves anything in the world but their love it was difficult and frustrating. She had fooled herself into thinking that Dan and her could make it because Blair and Chuck had. If Chuck and Blair could make it, anybody could, she had whispered night after night, clutching her pillow close to her chest as Dan slept on the couch.

"Dan and I, we barely talk anymore. We don't even sleep in the same bed, it's look the two of us are strangers. Dan just busies himself with his book and I pretend not to notice as I work for KC. I busy myself with attending to her every need while he ignores me. It's _hard_, our parents are going to have another child with each other," She explains, Nate's let go off her and her hands have been flying everywhere before finally falling onto her face and she flops down onto the couch.

"Serena. It's been bad from the very start, I've been here from the start. Believe me, I know." He tells her, his mind flittering back to the long phone calls while she was on her honeymoon.

"But god, I love him and we've worked so hard to get where we are now," She explains, her eyes hopeful. It's true, they'd worked so hard to get where they are now. Had tried and failed and then succeeded but Nate had a point. It has been bad from the start, it's been bad since Georgina re-entered Serena's life in her Junior year of high school.

"S, maybe it's time to admit that Dan and you just don't work anymore and trust me I hate saying this because you and Dan have been happy together and that's all I want your happiness and his happiness." It's no use though because the words are flying through Serena's mind and then out of it.

"You don't understand, do you?" She shouted abruptly, her blue eyes burning into his exquisite blue orbs. He gently sits down on the couch next to Serena, she curls her knees up to her chest and wraps her arms around them. She looks like a child, no older then five years old. Chuck's grabbed her ice-cream from out of her hands and has thrown it down the stairs. Her mother's got a new boyfriend and no time for Serena and Erik anymore.

"I do understand, Serena. You love Dan but you're not happy with him," He whispers, his fingers betraying him as they brush against his cheek. This is wrong, it's all so wrong. He shouldn't be feeling what he's feeling, he thinks he might still be in love with the blonde goddess in front of him but he forces himself to think of Jenny, to think of Dan. She nods her head limply, wondering how on earth everything had turned into this.

"I'm scared," She says under her breath after a beat. Nate's nodding his head along with her. She's terrified beyond belief but she knows what she needs to do, she needs to talk to Dan. Not break up with him, not divorce him but just sit down and talk to him. They need to talk, they've needed to talk for years. She hasn't been this scared in ages, the last time she felt this scared was when she accepted Dan's proposal. The two of them had only recently gotten back together after breaking up after another fight. She had smiled and grinned and gushed over how beautiful the ring was, it was plain and simple but darling. It was everything she had ever hoped for, she had kissed him as he slipped it onto her finger and thrown her arms around his neck. Everyone around them had clapped, it was Christmas and they all gushed about how romantic Dan was. Everyone except Blair, who had congratulated the two of them and had admired how Serena had suited the ring. Come to think of it, Nate hadn't been all that happy either, Chuck was of course not happy but he disapproved more of Dan then he did of anything else.

"Dan and I need to talk, we can sort this out right?" She questions Nate, her voice hopeful and her eyes shining bright. She watches as the smile slowly falls off of his face before he grins wider.

"The two of you have worked so long to get where you are now. Of _course _you can work it out!" He replies enthusiastically, no trail of sarcasm in his voice. He was just sad that two of his best friends would have to suffer through a marriage where nether one of them were completely happy. He knew Dan wasn't happy either. The two of them had shared many talks where Dan had complained about how much harder marriage was then he had expected it too be.

"Dan loves you so much, Serena." The words slip from off of his tongue in an effort to make the blonde happy, a warm, lazy smile floats across her face. She loves Dan, Dan loves her. It's meant to be, the two of them can work it out, he lies to himself. She's lying to herself as she repeats over and over to herself that her and Dan can get through this because the two of them have been over ever since the impending bundle of joy was announced.

"It's not going to work," She breaths after a minute or four of silence. Nate looks up from where his eyes had been previously attached to the T.V screen in front of him, she's looking at her fingers. At the rings on one finger, a small, beautiful diamond and a gold thin band. He had been drunk, a drunken mistake he had called it and he had been _so _guilty and they technically weren't together as he had reminded her. "He slept with someone else a few weeks ago, we had decided to take a break after the news of the new baby had come out. After about a week, he had gotten wasted and slept with someone else. He had called me straight away and had apologised for hours. I wasn't even that mad, we decided to try again but we didn't really try." She tells him, not lifting her eyes up from off of her hands.

Nate hadn't known _this. _Dan hadn't told him about it, he had left it out as he complained about his problems with marriage. He hadn't disclosed the information about how he had taken a break out of his marriage with his wife or about how while on that said break he had fallen into bed with somebody else. Surprisingly Serena didn't seem to mind, no tears fell from her eyes and her lower lip didn't even quiver. Before he could stop himself his lip was pressed against her cheek. It was a friendly kiss, nothing romantic about it. He had done it before, situations similar to this too all his other friends, to the golden girl sitting in front of him but it was just somehow different this time. _He's still in love with her_. If he was being honest with himself he never really stopped loving her, just pushed the thoughts into the back of his mind, buried them deep. Lost himself with other romances, consumed himself with work. He pulls back, his cheeks flushed a light pink, his gaze settles on the T.V screen once again. Her eyes bore into the side of his head.

"Do you remember that one summer when we were at the Hamptons, we must of been like fourteen and we were at the beach. Blair was busy catching up on her holiday assignments and finding new minions. Chuck was off god knows where, doing god knows what and we had decided to go for a swim? I had been so heartbroken over my latest failed relationship and you had cheered me up. I just remember that hug you gave me after we got out of the water, it had lingered longer then it should of and then we got ice-cream. It was one of the best days I've ever had," She explained, rambling on about past times where they had secretly been in love but could never embrace it. Her cheeks flush a bright red and her finger twirls around a lock of hair.

"I was so in love with you then. I always had been but you with Blair. I remember wanting you too look at me like you had looked at her when we had gotten home, full of this all consuming powerful love." She blushed again, the feelings weren't secrets that were hidden away in some drawer that was too never be opened. They were facts that they had both known then and both knew now.

"I did love you Serena. I loved you more then I loved Blair and it was wrong. Blair was my girlfriend, you were her best friend. So I tried my best to show Blair how much I loved her." He stated. The two of them fell into a comfortable silence, reminiscing of the past young love they shared and other old childhood memories. It was bittersweet.

"Do you remember when Blair used to make us play _Fairytales_. You would always be the Prince, she would always be the Princess, I would be stuck with being an ugly stepsister and Chuck would always be the evil monster intent on ruining everyone's happiness?" Serena laughs, her voice bouncing across the room. Nate nods his head, laughs about one of the times they had to play that particular game and then lets the comfortable silence engulf the room once more. Serena fidgets, bites her nails, looks around the room. She clearly isn't handling the silence like Nate thought she had been.

"How are you and Jenny?" She asks after a beat, her voice is soft like silk and sad like salty tears. He pauses, stops, backtracks, Jenny and him? His eyes briefly close, their last encounter still feeling rather grim in his mind. He doesn't remember what the fight was about but it had ended up with her in tears and fleeing towards the safety of work. The two of them had kissed and made up but it still felt rather sour in his mind.

"Not the greatest but not the worst. We just keep fighting over pointless things," He sighs, running a hand through his hair, shaking his head a little. Her smile is tight and she's rubbing his arm softly and then it feels as if everything's falling into place. His lips are on hers and their tongues are battling, dancing, _together._

* * *

**A\N: Eek, hope this was long enough! Sorry for the wait, this was one of my favourite things to write. I did want it longer but oh well, the drama is only just really starting. Reviews = love remember! **


	10. Confliction, I love you's and Goodbye's

**Title: **Heartbreakingly Perfect.

**Summary: **Serena's conflicted, once again. She loves Dan, she'll always love him but she also loves Nate. She's loved him since before she can remember, blue eyed, blonde haired, polo shirts, Vanderbilt drama. She's loved Archibald back when he loved Waldorf. We were left watching a Humphrey wed a Van Der Woodsen, not knowing what would become of everyone's fate. Post 6.1O. Pairings inside.

**Authors Note: **Hiya, updated the summary to avoid confusion of this being a Derena story - which it most certainly is not.

**Disclaimer: **I own nothing, nada, zip, zap.

* * *

She doesn't remember the moment she first fell in love with Nate, perhaps it was when she first met him but she knows that it wasn't then. She's always loved him, from the first moment she saw him but not _this _love. She guesses - a wild, crazy, guess, that it was when they were seven and at the zoo and it started pouring down with rain and he handed her his coat like a gentlemen out of those movies that Blair _just used to watch_. She had giggled, because she always giggled and had accepted his coat, throwing it over the top of her head and grabbing his arm and pulling him underneath the coat. They used it as a shield from the rain.

Her fingers flick to the next page of photographs, Blair's face smiling up at her, Chuck's arm thrown carelessly over Nate's. She's in the photo as well, her arms thrown around Blair and Nate, squishing all their faces together. Her fingers trace of the photo, she remembers that day. It was a week before she left, before everything got so screwed up. They had been spending the day at Chuck's suite, watching movies, mainly Audrey because Blair wouldn't have it any other way. Chuck and Nate were laughing the whole time, lighting up and getting high. Blair had frowned, told them to be quiet and recited the words that flowed out of Audrey's mouth as if she owned them. She hadn't been feeling the best that day and Blair had quoted "Has our beautiful blonde fallen?" Serena had laughed, rolled her eyes and had spent the rest of the day drinking herself into oblivion. The photo had been taken at a point where _everybody _was giggly, Blair had broken into the dom and had drowned three whole bottles before she could even register the fact in her mind. Serena remembers holding brunette hair back and whispering soothing ears in her best friend's ear as she vomited. It was hard for Serena to see her like that, she had been the only one who had known of her eating disorder at that time. Nate hadn't found out until Senior Year and Blair had stupidly told Chuck during their brief affair in Junior Year.

Her heart aches, her fingers itch too call her best friend and ask for advice but Blair had called her earlier, explaining that she knew what Serena was going through and that if she ever needed help she was there for her but Serena had refused her, claiming not to know what the other girl was talking about. She had pulled a classic Blair Waldorf in front of Blair Waldorf.

"I'm still a fucking child," She cursed, sending the album flying across the room. Her head falling back onto her old bed, she had left her and Dan's new residence shortly after Nate had barged in. Dan had guessed straight away that something was off but Serena had blown him off, a wave of her hand and a lie about needing to visit her mother. Even after all these years she doesn't know where her heart lies, where her head lies. She's as confused as she was when she had first slept with Nate, when she first arrived back after being away for a year.

"S." A voice floats into the room, Serena turns her head to see her best friend standing in the door way. A small smile twitches at the corner of Serena's lip but it's not real, not really. Blair falls onto the ground next to her and wraps her arms around her.

"Do you wanna talk?" Blair asks in a quiet voice, Serena shakes her head because there's nothing worse then trying to explain her feelings to somebody else when she doesn't even understand them herself. The two of them sit there in silence, arms locked together, Serena's head resting on Blair's shoulder. It's almost as if the two of them are fourteen and are finding the first year of high school a lot tougher then it should be.

"I love you, B." Serena whispers, her eyes fluttering close. She loves Blair with her whole heart and at least she'll have her if everything else burns up in flames and that's all she can really ask for.

* * *

"Jenny, are you awake?" Nate asks through the darkness, his fingers searching for her in the cold bed. He finds her side empty, he sighs and slips out of bed, wandering through the apartment looking for her. He finds her sitting on the couch, eyes trained on the screen, a rerun of some show playing on the screen, a cigarette dangling from out of her thin fingers.

"Jen," He says softly, her head snaps up at the sound of her name and a smile finds it's way onto her face. She pats the couch, motioning for him to join her. He hesitantly takes the seat next to her, lying his head on her legs. He plucks the cigarette from out of her fingers and places it in his mouth, the two of them have both been under a lot of stress and he really shouldn't mention the fact that he slept with her brother's wife. He had tossed and turned all night, trying to come up with what he should tell her.

"How's the Spectator? I feel like I've barely seen you between me at Waldorf Designs and you running The Spectator." She looks down at him, her fingers running through his hair. _This _is why he fell in love with her, this is what he misses. The calm feeling, the easy feeling, the simple love. He pauses for a few seconds, savoring the feeling that traps them, surrounds them.

"It's good, like really good but I would rather hear all about your new line coming out?" He prods, raising his eyebrows in the air. She giggles at his facial expressions, his mouth formed into a cheesy grin, his eyebrows up in the sky. She whacks him lightly across the chest, her cheeks flushing pink. She'll never get used to attention, never, despite the practice that she's had. It was like starting anew when she moved back to New York. She had changed so much in Hudson, it was only right that she would change again.

"Well as I've been promoted, it means that I am now head designer and we're currently working on a new Summer line. A lot of it is inspired by summery Audrey Hepburn, or so Blair claims anyway," Jenny rolls her eyes at this, she'll never understand Blair. Nate's heart warms up because for once, Jenny and Blair have been able to get along.

"So you and Blair, should I be jealous?" He teases, Jenny mock frowns, her nose crinkling up in disgust.

"As _if_," She imagines herself as Cher from off of _Clueless_ in that moment, "I would rather die than trade you in for Ms. I'm still better than you, Little J." Nate laughs, gathering Jenny in his arms. Serena was a mistake, a foolish, _drunken _mistake but he doesn't even know if the two of them had been drinking. It was a mistake nonetheless, his heart belongs to Jenny and that's where it will stay.

"Love you," He says lightly, his lips pressing lightly down onto her head. She giggles and pulls his lips down to hers.

"Better," She pouts, a giggle escaping her lips. It's as if she's an innocent fourteen year old again, a freshman being introduced to high society. She runs her hands though his hair and pulls him back towards her.

* * *

"Vanessa, you've never told me anything about you before we met," Barcelona lets the words escape his lips late one night, Vanessa's body is lying across the bed, a book in her hands. Her eyes flit up to Barcelona, who's eyes are closed contently, he's lying next to her. She sighs and shuts her book closed, knowing that this would be a long conversation.

"What do you want to know?" The question is laced with annoyance and a deep, heavy sigh follows the question. She doesn't want to talk about the past, it's a distant memory, filled with pain and heartbreak.

"Like, everything. Why don't you ever talk about it?" Barcelona asks, threading his fingers with hers. She wants to yank her hand away, turn her back on him like she had done so many times before but she couldn't go around walking around on eggshells for days on end, she couldn't lie anymore and hide the truth.

"I had moved away from New York for a bit and when I came back, my best friend Dan was dating like the most popular girl of the whole of New York and it seemed as if he was a whole different person. I became friends with her but I hated her friends which sort of became Dan's friends. I started dating this guy, Nate, who knew Dan's girlfriend, Serena and everything was fine until it flopped and all this other drama happened. I became someone I hated, I plotted and I planned and I schemed and then I ended up leaving New York and escaping here, but it all happened because of this website, Gossip Girl. She would spread nasty rumors about everyone and she did it all anonymously. It was revealed around five years ago that it was Dan, my _best friend_ Dan. I-I loved him," She pauses, waiting for Barcelona's reaction. His eyes were wide with fear and she flinched, he would ask about her scheming and then he would leave her.

"Ness," He sighs, untangling their fingers and running them through his hair. He slowly got out of bed and walked back in forth in their room, his mind running wild with thoughts and pictures of Vanessa _scheming_. He'd always hated that word, he'd grown up with liars and cheats and schemers for his family but he'd never gotten involved with any of it. He was an asshole, he'd always been one but he'd never been one to ruin other peoples lives.

"Tell me about what you did when you, when you _schemed_." He sneered the last worst with as much disgust as he could muster, Vanessa moved into a sitting up position. She folded her hands in her lap and let out another sigh, she didn't want him to know how truly evil she could be. She had always prided herself on being good, being better than all those park avenue princess's and prince's but in the end she had turned out just like them.

"I drugged Serena along with Dan's younger sister and another girl who hated her. I tried to _ruin_ her. She ended up in hospital and I felt so guilty, I then told Dan's father that it had been Jenny, Dan's little sister." She pauses once again, trying to regain her breathing to a normal pace. She hated who she had became, it hadn't been her, she had tried to reform herself in Spain and she had tried for the most part but along with reforming herself she had also lost herself. It was hard to explain.

"_You_ drugged someone!" Barcelona exclaims, a hand clamping over his mouth. Vanessa's head falls down onto the mass of pillows, it was over. Everything was over for her. Barcelona would leave her, she would be stuck in Spain with no friends and-

She would have to go back to New York but she knew that even if Barcelona decided to stay with her, which let's face it he wouldn't, she would have to go back sometime. If he broke up with her though, she would have to go straight away. She would need to escape and she had some sort of _friends _in New York. Rufus hadn't completely disowned her, had he? And Dan would forgive her, he would have too, he had been the anonymous blogger from their youth.

"Vanessa, I think I need some time to think." Barcelona's voice breaks the silence, cutting through it with a knife. She nods her head and wills the tears forming in her eyes to vanish but instead they fall from her eyes as she watches his retreating form. She curls up in a fetus position and cries her heart out, she regrets _everything_. It eats at her, claws at her, destroys her and she feels sick to her stomach.

Everything hurts, her whole body is on fire and she's shaking uncontrollably. She's never felt _this _much pain before, it crashes down on top of her and sends her over the edge. She cries until her eyes are dry, until she can't feel her throat anymore, until it's just a scratchy presence in her life. Every single thing she regrets, that she hates, that has made her feel one ounce of sadness falls down onto her. Everything comes crashing down upon her now frail body and the pain is enough to make her want to throw herself off of a bride. It hits her that she's alone, she has no friends, her boyfriend is gone, her family hasn't spoken to her in forever. She has _no one_. She's never really had anyone to begin with and the few people she did have she had lost rather quickly.

It was _all _over. Everything she had ever worked for was over, her film carer had been shot to hell after she had released a crappy short film for a special viewing last year. She had been dubbed as "That girl who had tried but had failed." She falls asleep after hours of crying and when she wakes up in the morning she throws everything into a suitcase and books a ticket for the first plane out to New York, which means she had to spend every cent she owns on that ticket.

* * *

**A\N: Oh wow, I forgot all about this and so I quickly wrote something and it sucks, like oh my god the Vanessa\Barcelona bit isn't what I wanted to happen but it sort of just all came out as I was writing. However what happens to Vanessa at the end is something I actually get a lot but it isn't everything crashing down at once, it's like every little tiny small detail crashing down upon me.  
**


	11. Author's Note: Highly Important

I've thought over what every has said and I've decided not to take a break. Why should I let some scared anonymous user define what I should and should not do? It just sometimes gets to me, you know. It isn't the first message and it won't be the last but I will be going on, sorry for the scare for those who actually care.


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